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【结 构 式】

【分子编号】29017

【品名】(E)-N-[4-(acetamido)phenyl]-3-ethoxy-2-propenamide

【CA登记号】

【 分 子 式 】C13H16N2O3

【 分 子 量 】248.28172

【元素组成】C 62.89% H 6.5% N 11.28% O 19.33%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

OPC-8212 is obtained through the piperazine ring formation method from bis(beta-bromoethyl)amine hydrobromide and 6-amino-3,4-dihydro-2(1H)-quinolinone (V) to give (VI). (V) is synthesized using the ring closure reaction of p-acetylamino-beta-ethoxyacryloanilide (II). p-Acetylaminoaniline (I) is converted to (II) by treatment with beta-ethoxyacryloyl chloride and afterwards cyclized in the presence of sulfuric acid to give 6-acetylamino-2-(1H)-quinolinone (III). Hydrogenation of (III) over 10% palladium on charcoal gives 6-acetylamino-3,4-dihydro-2(1H)-quinolinone (IV). Hydrolysis of (IV) gives 6-amino-3,4-dihydro-2(1H)-quinolinone (V). OPC-8212 is obtained by adding 3,4-dimethoxybenzyl chloride (VII) to (VI).

1 Nakagawa, K.; Osumi, T.; Shimizu, T.; Niimi, K.; Physicochemical properties and stabilities of a new positive inotropic agent, OPC 8212. Arzneim-Forsch Drug Res 1984, 34, 3A, 334-341.
2 Yo, E.; Ogawa, H.; Yamashita, S.; Tominaga, M.; Nakagawa, K.; Yabuuchi, Y.; Studies on positive inotropic agents. I. Synthesis of 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone and related compounds. Chem Pharm Bull 1984, 32, 6, 2100.
3 Mannhold, R.; OPC-8212. Drugs Fut 1985, 10, 1, 28.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 20616 (E)-3-ethoxy-2-propenoyl chloride 99471-66-6 C5H7ClO2 详情 详情
(B) 29020 2-bromo-N-(2-bromoethyl)-1-ethanamine C4H9Br2N 详情 详情
(I) 29016 N-(4-aminophenyl)acetamide 122-80-5 C8H10N2O 详情 详情
(II) 29017 (E)-N-[4-(acetamido)phenyl]-3-ethoxy-2-propenamide C13H16N2O3 详情 详情
(III) 29018 N-(2-oxo-1,2-dihydro-6-quinolinyl)acetamide C11H10N2O2 详情 详情
(IV) 29019 N-(2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)acetamide C11H12N2O2 详情 详情
(V) 29022 6-amino-3,4-dihydro-2(1H)-quinolinone C9H10N2O 详情 详情
(VI) 29021 6-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone C13H17N3O 详情 详情
(VII) 13438 3,4-Dimethoxybenzoyl chloride 3535-37-3 C9H9ClO3 详情 详情
Extended Information